Sodium hydride → 2-Butyl-5-cyano-4-(1-hydroxy-1-methylpropyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole

HRID 52897Notes

Reaction equation

HRID 52897 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([C:15]#[N:16])=[C:8]([C:10]([OH:14])([CH3:13])[CH2:11][CH3:12])[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[C:19]([N:38]1[C:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[C:49]2[CH:56]=[CH:55][C:52]([CH2:53]Br)=[CH:51][CH:50]=2)=[N:41][N:40]=[N:39]1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:1]([C:5]1[N:6]([CH2:53][C:52]2[CH:51]=[CH:50][C:49]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=3[C:42]3[N:38]([C:19]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:39]=[N:40][N:41]=3)=[CH:56][CH:55]=2)[C:7]([C:15]#[N:16])=[C:8]([C:10]([OH:14])([CH3:13])[CH2:11][CH3:12])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 178441653HCID 178441653, compound

Product 1

HCID 190363492-Butyl-5-cyano-4-(1-hydroxy-1-methylpropyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazoleYield 72%

Procedure

Following a procedure similar to that described in Example 18(a), but using 465 mg of 2-butyl-5-cyano-4-(1-hydroxy-1-methylpropyl)imidazole (prepared as described in Preparation 19), 92 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) and 1.11 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide, 1.00 g of the title compound was obtained as a gum.

Sources & evidence

ORD record
ord-b27d8cf83e9f4531990ce6bd7de2c66c
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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